This invention relates to ortho(sulfonyl)oxybenzene sulfonamides and their use as herbicides.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (I), and their use as general or selective herbicides: ##STR1## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA0 R.sub.4 is hydrogen, fluorine, chlorine, bromine or methyl; PA0 R.sub.5 is hydrogen, fluorine, chlorine, bromine, methyl or methoxy; PA0 R.sub.7 is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atoms or alkoxy of 1-2 carbon atom; PA0 R.sub.8 is hydrogen, methyl, chlorine or bromine; PA0 R.sub.9 and R.sub.10 are independently hydrogen, methyl, chlorine or bromine; PA0 W and Q are independently oxygen or sulfur; PA0 n is 0, 1 or 2; PA0 X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbon atoms, trifluoromethyl, CH.sub.3 S-- or CH.sub.3 OCH.sub.2 --; and PA0 Y is methyl or methoxy; or their agriculturally suitable salts; provided that: PA0 Q is O or NR.sub.5 ; PA0 R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 or ##STR6## R.sub.2 is H, F, Cl, Br, OCH.sub.3, NO.sub.2, CF.sub.3 or C.sub.1 -C.sub.2 alkyl; PA0 R.sub.3 is H, F, Cl, Br or CH.sub.3 ; PA0 R.sub.4 is H, CH.sub.3 or OCH.sub.3 ; PA0 R.sub.5 is C.sub.1 -C.sub.4 alkyl; PA0 R.sub.6 and R.sub.7 are independently H, F, Cl, Br, CH.sub.3, CF.sub.3, NO.sub.2 or OCH.sub.3 ; PA0 A is ##STR7## X is NH.sub.2, N(CH.sub.3).sub.2, NHCH.sub.3, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br, CH.sub.2 OCH.sub.3, CH.sub.2 OCH.sub.2 CH.sub.3, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.2 alkylthio, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, OCH.sub.2 CH.sub.2 OCH.sub.3 or C.sub.2 -C.sub.4 alkoxy substituted with 1-3 atoms of F, Cl or Br; PA0 n is 1 or 2; PA0 Y is H, CH.sub.3, OCH.sub.3 or Cl; PA0 X.sub.1 is O or CH.sub.2 ; PA0 Y.sub.1 is H, CH.sub.3, OCH.sub.3 or Cl; PA0 X.sub.2 and Y.sub.2 are independently CH.sub.3 or OCH.sub.3 ; and PA0 Z is CH, N, CCH.sub.3, CBr, CCl, CF, CI, CC.sub.2 H.sub.5, CCH.sub.2 CH.sub.2 Cl or CCH.sub.2 CH.dbd.CH.sub.2 ; PA0 (1) when Y is Cl, then Z is other than N and X is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, CH.sub.3 or OCH.sub.3 ; PA0 (2) when Y is H, then X is OCH.sub.3, CH.sub.3 or CH.sub.2 OCH.sub.3, and Z is other than N; PA0 (3) when W is S, then R.sub.4 is H; and PA0 (4) when R.sub.4 is OCH.sub.3, then Q is O. PA0 (1) Compounds of the generic scope where R.sub.5 is CH.sub.3, W is O, and R.sub.4 is H or CH.sub.3 ; PA0 (2) Compounds of Preferred (1) where R.sub.1 is C.sub.1 -C.sub.4 alkyl, CF.sub.3, CH.sub.2 CH.sub.2 OCH.sub.3 or CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 ; PA0 (3) Compounds of Preferred (2) where R.sub.2 is H or Cl; PA0 (4) Compounds of Preferred (3) where R.sub.3 is H; PA0 (5) Compounds of Preferred (4) where PA0 (6) Compounds of Preferred (5) where R.sub.4 is H; PA0 (7) Compounds of Preferred (6) where X and Y are independently CH.sub.3 or OCH.sub.3, and R.sub.1 is CH.sub.3 ; and PA0 (8) Compounds of the generic scope where PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-hydroxy-5-chlorobenzenesul fonamide methanesulfonate; PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate; PA0 2-hydroxy-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfona mide, methanesulfonate; and PA0 N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, methanesulfonate. PA0 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfona mide, methanesulfonate; PA0 2-hydroxy-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesu lfonamide, methanesulfonate; PA0 N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonam ide, methanesulfonate; PA0 N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)(methyl)aminocarbonyl]-2-hydroxybenzen esulfonamide, methanesulfonate; PA0 N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-hydroxybenzenesulfonamide, 1-propanesulfonate, which shows selectively on rice and corn; and PA0 2-hydroxy-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesu lfonamide, 1-propanesulfonate, which shows selectivity on soybeans. PA0 Q is O or NR.sub.5 ; PA0 R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3, or ##STR11## R.sub.2 is H, F, Cl, Br, OCH.sub.3, NO.sub.2 or C.sub.1 -C.sub.2 alkyl; R.sub.3 is H, F, Cl, Br or CH.sub.3 ; PA0 R.sub.5 is C.sub.1 -C.sub.4 alkyl; and PA0 R.sub.6 and R.sub.7 are independently H, F, Cl, Br, CH.sub.3, CF.sub.3, NO.sub.2 or OCH.sub.3. PA0 (1) Compounds of Formula II where Q is O, R.sub.2 and R.sub.3 are H, R.sub.1 is CH.sub.3 or CF.sub.3, and W is O. PA0 R.sub.1 is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkyl substituted with 1-3 atoms of F, Cl or Br, CH.sub.2 CH.sub.2 OCH.sub.3, CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3, or ##STR13## R.sub.2 is H, F, Cl, Br, OCH.sub.3, NO.sub.2 or C.sub.1 -C.sub.2 alkyl; R.sub.3 is H, F, Cl, Br or OCH.sub.3 ; PA0 R.sub.5 is C.sub.1 -C.sub.4 alkyl; PA0 R.sub.6 and R.sub.7 are independently H, F, Cl, Br, CH.sub.3, CF.sub.3, NO.sub.2 or OCH.sub.3 ; and PA0 Z is CH or N.
Compounds of Formula (II), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974): ##STR2## wherein R is pyridyl.
In U.S. Pat. No. 4,127,405, compounds are disclosed of the general formula: ##STR3## wherein R.sub.1 is ##STR4## R.sub.3 and R.sub.6 are independently hydrogen, fluorine, chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4 carbon atoms, nitro, trifluoromethyl, cyano, CH.sub.3 S(O).sub.n --or CH.sub.3 CH.sub.2 S(O).sub.n --;
(a) when R.sub.5 is other than hydrogen, at least one of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 is other than hydrogen and at least two of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be hydrogen; PA1 (b) when R.sub.5 is hydrogen and all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 are other than hydrogen, then all of R.sub.3, R.sub.4, R.sub.6 and R.sub.7 must be either chlorine or methyl; and PA1 (c) when R.sub.3 and R.sub.7 are both hydrogen, at least one of R.sub.4, R.sub.5 or R.sub.6 must be hydrogen. PA1 R.sub.1 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; PA1 Q is O; PA1 A is ##STR8## and Z is CH or N; PA1 Q is ##STR9## R.sub.5 is CH.sub.3 or CH.sub.3 CH.sub.2 ; R.sub.1 is C.sub.1 -C.sub.3 alkyl or CF.sub.3 ; PA1 R.sub.2 and R.sub.3 are H; PA1 X is CH.sub.3, OCH.sub.3, N(CH.sub.3), CH.sub.2 OCH.sub.3, OCH.sub.2 CH.sub.3 or OCH.sub.2 CF.sub.3 ; PA1 Y is CH.sub.3, OCH.sub.3 or Cl; and PA1 Z is CH or N.
In particular, the patent discloses ortho-substituted compounds wherein the substitution is C.sub.1 -C.sub.4 alkyl.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food needs, such as soybeans, corn, wheat and the like. The current population explosion and concomitant world food shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of valuable crops by killing, or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing, or inhbiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. However, the need exists for still more effective herbicides that destroy or retard weeds without causing significant damage to useful crops.